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Literature DB >> 20507088

Intramolecular Fe(II)-catalyzed N-O or N-N bond formation from aryl azides.

Benjamin J Stokes¹, Carl V Vogel, Linda K Urnezis, Minjie Pan, Tom G Driver.

Abstract

Iron(II) bromide catalyzes the transformation of aryl and vinyl azides with ketone or methyl oxime substituents into 2,1-benzisoxazoles, indazoles, or pyrazoles through the formation of an N-O or N-N bond. This transformation tolerates a variety of different functional groups to facilitate access to a range of benzisoxazoles or indazoles. The unreactivity of the Z-methyloxime indicates that N-heterocycle formation occurs through a nucleophilic attack of the ketone or oxime onto an activated planar iron azide complex.

Entities: Chemical Disease Gene

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Year: 2010 PMID： 20507088 PMCID： PMC2913475 DOI： 10.1021/ol101040p

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

21 in total

1. Highly enantioselective iron-catalyzed sulfide oxidation with aqueous hydrogen peroxide under simple reaction conditions.

Authors: Julien Legros; Carsten Bolm
Journal: Angew Chem Int Ed Engl Date: 2004-08-13 Impact factor: 15.336

2. Vanadium-catalyzed sulfur oxidation/kinetic resolution in the synthesis of enantiomerically pure alkyl aryl sulfoxides.

Authors: Carmelo Drago; Lorenzo Caggiano; Richard F W Jackson
Journal: Angew Chem Int Ed Engl Date: 2005-11-11 Impact factor: 15.336

3. Structure-activity studies of a novel series of 5,6-fused heteroaromatic ureas as TRPV1 antagonists.

Authors: Irene Drizin; Arthur Gomtsyan; Erol K Bayburt; Robert G Schmidt; Guo Zhu Zheng; Richard J Perner; Stanley DiDomenico; John R Koenig; Sean C Turner; Tammie K Jinkerson; Brian S Brown; Ryan G Keddy; Heath A McDonald; Prisca Honore; Carol T Wismer; Kennan C Marsh; Jill M Wetter; James S Polakowski; Jason A Segreti; Michael F Jarvis; Connie R Faltynek; Chih-Hung Lee
Journal: Bioorg Med Chem Date: 2006-04-18 Impact factor: 3.641

4. New practical synthesis of indazoles via condensation of o-fluorobenzaldehydes and their O-methyloximes with hydrazine.

Authors: Kirill Lukin; Margaret C Hsu; Dilinie Fernando; M Robert Leanna
Journal: J Org Chem Date: 2006-10-13 Impact factor: 4.354

5. Copper and silver complexes containing organic azide ligands: syntheses, structures, and theoretical investigation of [HB(3,5-(CF3)2Pz)3]CuNNN(1-Ad) and [HB(3,5-(CF3)2Pz)3]AgN(1-Ad)NN (where Pz = pyrazolyl and 1-Ad = 1-adamantyl).

Authors: H V Dias; S A Polach; S K Goh; E F Archibong; D S Marynick
Journal: Inorg Chem Date: 2000-08-21 Impact factor: 5.165

6. Fe(II)-catalyzed imidation of allyl sulfides and subsequent

Authors:
Journal: J Org Chem Date: 2000-04-21 Impact factor: 4.354

7. A novel synthesis of 2-aryl-2H-indazoles via a palladium-catalyzed intramolecular amination reaction.

Authors: J J Song; N K Yee
Journal: Org Lett Date: 2000-02-24 Impact factor: 6.005

8. Organic azides: an exploding diversity of a unique class of compounds.

Authors: Stefan Bräse; Carmen Gil; Kerstin Knepper; Viktor Zimmermann
Journal: Angew Chem Int Ed Engl Date: 2005-08-19 Impact factor: 15.336

9. Rhodium-catalyzed imination of sulfoxides and sulfides: efficient preparation of N-unsubstituted sulfoximines and sulfilimines.

Authors: Hiroaki Okamura; Carsten Bolm
Journal: Org Lett Date: 2004-04-15 Impact factor: 6.005

10. Iron(II)-catalyzed sulfimidation and [2,3]-sigmatropic rearrangement of propargyl sulfides with tert-butoxycarbonyl azide. Access to N-allenylsulfenimides.

Authors: James P Bacci; Kevin L Greenman; David L Van Vranken
Journal: J Org Chem Date: 2003-06-13 Impact factor: 4.354

16 in total

10. General synthesis of 2,1-benzisoxazoles (anthranils) from nitroarenes and benzylic C-H acids in aprotic media promoted by combination of strong bases and silylating agents.

Authors: Michał Wiȩcław; Mariusz Bobin; Andrzej Kwast; Robert Bujok; Zbigniew Wróbel; Krzysztof Wojciechowski
Journal: Mol Divers Date: 2015-08-11 Impact factor: 2.943

Intramolecular Fe(II)-catalyzed N-O or N-N bond formation from aryl azides.

1. Highly enantioselective iron-catalyzed sulfide oxidation with aqueous hydrogen peroxide under simple reaction conditions.

2. Vanadium-catalyzed sulfur oxidation/kinetic resolution in the synthesis of enantiomerically pure alkyl aryl sulfoxides.

3. Structure-activity studies of a novel series of 5,6-fused heteroaromatic ureas as TRPV1 antagonists.

4. New practical synthesis of indazoles via condensation of o-fluorobenzaldehydes and their O-methyloximes with hydrazine.

5. Copper and silver complexes containing organic azide ligands: syntheses, structures, and theoretical investigation of [HB(3,5-(CF3)2Pz)3]CuNNN(1-Ad) and [HB(3,5-(CF3)2Pz)3]AgN(1-Ad)NN (where Pz = pyrazolyl and 1-Ad = 1-adamantyl).

6. Fe(II)-catalyzed imidation of allyl sulfides and subsequent

7. A novel synthesis of 2-aryl-2H-indazoles via a palladium-catalyzed intramolecular amination reaction.

8. Organic azides: an exploding diversity of a unique class of compounds.

9. Rhodium-catalyzed imination of sulfoxides and sulfides: efficient preparation of N-unsubstituted sulfoximines and sulfilimines.

10. Iron(II)-catalyzed sulfimidation and [2,3]-sigmatropic rearrangement of propargyl sulfides with tert-butoxycarbonyl azide. Access to N-allenylsulfenimides.

Review 1. Heteroatom-Heteroatom Bond Formation in Natural Product Biosynthesis.

Review 2. Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

3. One-pot, two-step cascade synthesis of quinazolinotriazolobenzodiazepines.

4. Diverting Reactive Intermediates Toward Unusual Chemistry: Unexpected Anthranil Products from Davis-Beirut Reaction.

5. A Biphilic Phosphetane Catalyzes N-N Bond-Forming Cadogan Heterocyclization via P^III/P^V═O Redox Cycling.

6. Palladium-catalyzed Hiyama cross-coupling of aryltrifluorosilanes with aryl and heteroaryl chlorides.

7. Nitrene-mediated intermolecular N-N coupling for efficient synthesis of hydrazides.

8. Iron(II) bromide-catalyzed intramolecular C-H bond amination [1,2]-shift tandem reactions of aryl azides.

9. Rhodium(III)-catalyzed indazole synthesis by C-H bond functionalization and cyclative capture.

10. General synthesis of 2,1-benzisoxazoles (anthranils) from nitroarenes and benzylic C-H acids in aprotic media promoted by combination of strong bases and silylating agents.